$130+ Cheap flights from Midland (MAF) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — SJU
Mar 8 — Mar 151
1 adult, Economy
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Find cheap flights from Midland to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midland to Caribbean
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Cheapest flights from Midland to CaribbeanExplore the most affordable flight options available from Midland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 6, 2026.
Explore the most affordable flight options available from Midland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 6, 2026.
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:24 pm
MAF
- SJU
1 stop7h 08m
American Airlines
Fri 5/1511:59 pm
SJU
- MAF
1 stop10h 43m
American Airlines
Deal found 2/3![American Airlines logo]()
$260
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:00 am
MAF
- SJU
1 stop7h 36m
United Airlines
Tue 3/107:05 am
SJU
- MAF
2 stops16h 10m
United Airlines
Deal found 2/3![United Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:00 pm
MAF
- SJU
2 stops9h 25m
Southwest
Fri 5/152:00 pm
SJU
- MAF
2 stops10h 10m
Southwest
Deal found 2/3![Southwest logo]()
$382
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:00 am
MAF
- SJU
1 stop7h 36m
United Airlines
Thu 2/267:40 am
SJU
- MAF
1 stop8h 08m
United Airlines
Deal found 2/3![United Airlines logo]()
$383
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:43 am
MAF
- SJU
1 stop9h 43m
United Airlines
Wed 3/43:46 pm
SJU
- MAF
1 stop9h 29m
United Airlines
Deal found 2/3![United Airlines logo]()
$390
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/311:45 am
MAF
- SJU
2 stops10h 50m
Southwest
Tue 3/106:40 am
SJU
- MAF
2 stops11h 30m
Southwest
Deal found 2/3![Southwest logo]()
$422
This American Airlines deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:31 pm
MAF
- SJU
1 stop16h 32m
American Airlines
Tue 9/152:05 pm
SJU
- MAF
2 stops10h 36m
American Airlines
Deal found 2/5![American Airlines logo]()
$433
This United Airlines deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:11 pm
MAF
- SJU
1 stop9h 18m
United Airlines
Tue 6/21:40 pm
SJU
- MAF
1 stop9h 19m
United Airlines
Deal found 2/5![United Airlines logo]()
$441
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/11:00 pm
MAF
- SJU
2 stops9h 25m
Southwest
Mon 6/86:00 am
SJU
- MAF
1 stop8h 55m
Southwest
Deal found 2/4![Southwest logo]()
$473
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:20 pm
MAF
- MBJ
2 stops17h 10m
American Airlines
Sun 8/3010:25 am
MBJ
- MAF
2 stops13h 36m
American Airlines
Deal found 2/3![American Airlines logo]()
$597
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/77:03 pm
MAF
- MBJ
1 stop17h 02m
United Airlines
Sat 3/144:14 pm
MBJ
- MAF
2 stops19h 12m
United Airlines
Deal found 2/3![United Airlines logo]()
$630
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/115:15 am
MAF
- MBJ
2 stops9h 40m
Southwest
Tue 6/1611:45 am
MBJ
- MAF
2 stops11h 15m
Southwest
Deal found 2/3![Southwest logo]()
$655
Best flights from Midland to CaribbeanDiscover carefully curated flight deals from Midland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 6, 2026.
Discover carefully curated flight deals from Midland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 6, 2026.
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:16 pm
MAF
- SJU
2 stops13h 57m
American Airlines
Fri 5/1511:59 pm
SJU
- MAF
1 stop10h 43m
American Airlines
Deal found 2/3![American Airlines logo]()
$260
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:00 pm
MAF
- SJU
2 stops9h 25m
Southwest
Fri 5/152:00 pm
SJU
- MAF
2 stops10h 10m
Southwest
Deal found 2/3![Southwest logo]()
$382
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:00 am
MAF
- SJU
1 stop7h 36m
United Airlines
Thu 2/267:40 am
SJU
- MAF
1 stop8h 08m
United Airlines
Deal found 2/3![United Airlines logo]()
$383
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:07 pm
MAF
- SJU
1 stop7h 19m
United Airlines
Wed 3/43:46 pm
SJU
- MAF
1 stop9h 29m
United Airlines
Deal found 2/2![United Airlines logo]()
$390
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/311:45 am
MAF
- SJU
2 stops10h 50m
Southwest
Tue 3/106:40 am
SJU
- MAF
2 stops11h 30m
Southwest
Deal found 2/3![Southwest logo]()
$422
This United Airlines deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:11 pm
MAF
- SJU
1 stop9h 18m
United Airlines
Tue 6/21:40 pm
SJU
- MAF
1 stop9h 19m
United Airlines
Deal found 2/5![United Airlines logo]()
$441
This American Airlines deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/226:00 am
MAF
- SDQ
2 stops15h 53m
American Airlines
Sun 3/294:03 pm
SDQ
- MAF
2 stops20h 50m
American Airlines
Deal found 2/4![American Airlines logo]()
$685
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/115:15 am
MAF
- MBJ
2 stops9h 40m
Southwest
Tue 6/1611:45 am
MBJ
- MAF
2 stops11h 15m
Southwest
Deal found 2/3![Southwest logo]()
$655
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/77:03 pm
MAF
- MBJ
1 stop17h 02m
United Airlines
Sat 3/144:14 pm
MBJ
- MAF
2 stops19h 12m
United Airlines
Deal found 2/3![United Airlines logo]()
$630
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:27 pm
MAF
- MBJ
2 stops15h 15m
American Airlines
Tue 6/1612:47 pm
MBJ
- MAF
1 stop8h 53m
American Airlines
Deal found 2/3![American Airlines logo]()
$700
This American Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:48 pm
MAF
- SDQ
2 stops17h 31m
American Airlines
Thu 7/237:38 pm
SDQ
- MAF
2 stops16h 30m
American Airlines
Deal found 2/6![American Airlines logo]()
$729
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/232:56 pm
MAF
- AUA
2 stops20h 54m
United Airlines
Thu 2/265:50 pm
AUA
- MAF
2 stops21h 09m
United Airlines
Deal found 2/2![United Airlines logo]()
$742
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/205:07 pm
MAF
- SXM
2 stops18h 26m
United Airlines
Wed 4/223:50 pm
SXM
- MAF
2 stops18h 04m
United Airlines
Deal found 2/2![United Airlines logo]()
$748
Last-minute flights from Midland to CaribbeanDiscover last-minute flight deals from Midland to Caribbean. Data last updated February 6, 2026 and is based on user searches.
Discover last-minute flight deals from Midland to Caribbean. Data last updated February 6, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/146:20 pm
MAF
- SJU
2 stops13h 40m
American Airlines
Fri 2/2010:50 am
SJU
- MAF
2 stops13h 59m
American Airlines
Deal found 2/5![American Airlines logo]()
$551
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/169:43 am
MAF
- SJU
1 stop9h 43m
United Airlines
Fri 2/203:46 pm
SJU
- MAF
1 stop9h 29m
United Airlines
Deal found 2/3![United Airlines logo]()
$523
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:00 am
MAF
- SJU
1 stop7h 36m
United Airlines
Thu 2/267:40 am
SJU
- MAF
1 stop8h 08m
United Airlines
Deal found 2/3![United Airlines logo]()
$383
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/232:56 pm
MAF
- AUA
2 stops20h 54m
United Airlines
Thu 2/265:50 pm
AUA
- MAF
2 stops21h 09m
United Airlines
Deal found 2/2![United Airlines logo]()
$742
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:07 pm
MAF
- SJU
1 stop7h 19m
United Airlines
Wed 3/43:46 pm
SJU
- MAF
1 stop9h 29m
United Airlines
Deal found 2/2![United Airlines logo]()
$390
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:00 am
MAF
- SJU
1 stop7h 36m
United Airlines
Tue 3/107:05 am
SJU
- MAF
2 stops16h 10m
United Airlines
Deal found 2/3![United Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/311:45 am
MAF
- SJU
2 stops10h 50m
Southwest
Tue 3/106:40 am
SJU
- MAF
2 stops11h 30m
Southwest
Deal found 2/3![Southwest logo]()
$422
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
MAF
- SJU
1 stop15h 31m
American Airlines
Tue 3/103:12 pm
SJU
- MAF
1 stop18h 36m
American Airlines
Deal found 2/3![American Airlines logo]()
$498
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/77:03 pm
MAF
- MBJ
1 stop17h 02m
United Airlines
Sat 3/144:14 pm
MBJ
- MAF
2 stops19h 12m
United Airlines
Deal found 2/3![United Airlines logo]()
$630
This American Airlines deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/226:00 am
MAF
- SDQ
2 stops15h 53m
American Airlines
Sun 3/294:03 pm
SDQ
- MAF
2 stops20h 50m
American Airlines
Deal found 2/4![American Airlines logo]()
$685
One-way flights from Midland to CaribbeanSearch for one-way flight options from Midland to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 6, 2026.
Search for one-way flight options from Midland to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 6, 2026.
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:24 pm
MAF
- SJU
1 stop7h 08m
American Airlines
Deal found 2/3![American Airlines logo]()
$130
This American Airlines deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/75:23 pm
MAF
- MBJ
2 stops17h 32m
American Airlines
Deal found 2/5![American Airlines logo]()
$237
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/135:23 pm
MAF
- SJU
1 stop10h 09m
American Airlines
Deal found 2/3![American Airlines logo]()
$240
This United Airlines deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/135:23 pm
MAF
- SJU
2 stops26h 11m
United Airlines
Deal found 2/4![United Airlines logo]()
$431
Find flight deals from Midland to Caribbean
Keep the following information in mind while searching for Midland to Caribbean flight deals. Data was last updated February 6, 2026.
Round-trip from | $260 (American Airlines) |
|---|---|
One-way from | $130 (American Airlines) |
Popular in | July |
Cheapest in | April |
Average price | $764 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 6, 2026.
Use the filters below to find and compare flights from Midland to Caribbean that are best for you.
Fly from
Midland
Fly to
Caribbean
Route
Depart
Return
Price
MidlandSan Juan
MAF - SJU
MAFSJU
Midland Intl
Mon 5/11
6:16 pm-9:13 am
2 stops13h 57m
San Juan Luis Munoz Marin Intl
Fri 5/15
11:59 pm-9:42 am
1 stop10h 43m
$260
MidlandSan Juan
MAF - SJU
MAFSJU
Midland Intl
Mon 5/11
1:00 pm-11:25 pm
2 stops9h 25m
San Juan Luis Munoz Marin Intl
Fri 5/15
2:00 pm-11:10 pm
2 stops10h 10m
$382
MidlandSan Juan
MAF - SJU
MAFSJU
Midland Intl
Mon 2/23
7:00 am-4:36 pm
1 stop7h 36m
San Juan Luis Munoz Marin Intl
Thu 2/26
7:40 am-1:48 pm
1 stop8h 08m
$383
MidlandSan Juan
MAF - SJU
MAFSJU
Midland Intl
Mon 3/2
12:07 pm-9:26 pm
1 stop7h 19m
San Juan Luis Munoz Marin Intl
Wed 3/4
3:46 pm-11:15 pm
1 stop9h 29m
$390
MidlandSan Juan
MAF - SJU
MAFSJU
Midland Intl
Tue 3/3
11:45 am-12:35 am
2 stops10h 50m
San Juan Luis Munoz Marin Intl
Tue 3/10
6:40 am-5:10 pm
2 stops11h 30m
$422
MidlandSan Juan
MAF - SJU
MAFSJU
Midland Intl
Sat 5/30
7:11 pm-5:29 am
1 stop9h 18m
San Juan Luis Munoz Marin Intl
Tue 6/2
1:40 pm-9:59 pm
1 stop9h 19m
$441
MidlandMontego Bay
MAF - MBJ
MAFMBJ
Midland Intl
Sat 3/7
7:03 pm-1:05 pm
1 stop17h 02m
Montego Bay Sangster Intl
Sat 3/14
4:14 pm-11:26 am
2 stops19h 12m
$630
MidlandMontego Bay
MAF - MBJ
MAFMBJ
Midland Intl
Thu 6/11
5:15 am-2:55 pm
2 stops9h 40m
Montego Bay Sangster Intl
Tue 6/16
11:45 am-11:00 pm
2 stops11h 15m
$655
MidlandSanto Domingo
MAF - SDQ
MAFSDQ
Midland Intl
Sun 3/22
6:00 am-10:53 pm
2 stops15h 53m
Santo Domingo Las Americas
Sun 3/29
4:03 pm-11:53 am
2 stops20h 50m
$685
MidlandMontego Bay
MAF - MBJ
MAFMBJ
Midland Intl
Thu 6/11
8:27 pm-11:42 am
2 stops15h 15m
Montego Bay Sangster Intl
Tue 6/16
12:47 pm-9:40 pm
1 stop8h 53m
$700
Showing 1-10 of 17 results
Best time to book a flight from Midland to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Midland with our price prediction graph.
MAF-SJU
MAF-MBJ
MAF-SDQ
MAF-AUA
MAF-SXM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Midland to Caribbean
MAF-0CB
MAF-SJU
MAF-MBJ
MAF-SDQ
MAF-AUA
What is the cheapest month to book a flight from Midland to Caribbean?
Currently, April is the cheapest month in which you can book a flight from Midland to Caribbean (average of $247). Flying from Midland to Caribbean in July is currently the most expensive (average of $644). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated February 6, 2026.
Read through reviews of airlines operating flights from Midland to Caribbean, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
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Alternative routes for Midland to Caribbean
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Top 3 airlines flying from Midland to Caribbean
Discover the top 3 airlines that operate flights from Midland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$246 | Average$529 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$307 | Average$625 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$520 | Average$605 | FlexibilityNo cancel fee | On-time63% |